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WO1999025191A1 - Procede permettant d'induire une tolerance a la tension dans des matieres vegetales - Google Patents

Procede permettant d'induire une tolerance a la tension dans des matieres vegetales Download PDF

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Publication number
WO1999025191A1
WO1999025191A1 PCT/AU1998/000949 AU9800949W WO9925191A1 WO 1999025191 A1 WO1999025191 A1 WO 1999025191A1 AU 9800949 W AU9800949 W AU 9800949W WO 9925191 A1 WO9925191 A1 WO 9925191A1
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Prior art keywords
plants
active compounds
plant material
plant
loweralkyl
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English (en)
Inventor
Tissa Senaratna
Darren Touchell
Eric Bunn
Kingsley Dixon
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King's Park Board
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King's Park Board
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Priority to AU11366/99A priority Critical patent/AU1136699A/en
Publication of WO1999025191A1 publication Critical patent/WO1999025191A1/fr
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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/10—Aromatic or araliphatic carboxylic acids, or thio analogues thereof; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
    • A01N37/38—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
    • A01N37/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system having at least one carboxylic group or a thio analogue, or a derivative thereof, and one oxygen or sulfur atom attached to the same aromatic ring system
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
    • A01N41/04—Sulfonic acids; Derivatives thereof

Definitions

  • the present invention relates to a method for inducing stress tolerance in plant material through the use of active compounds such as benzoic acid, salicylic acid or a functional derivative thereof.
  • Plant life is susceptible to damage from stress associated with variations in temperature and moisture, injurious chemicals and combinations, and biological attack. Flowers, leaves, and other portions from plants that are cut also rapidly lose their fresh appearance due to the stress caused by such cutting. Substantial efforts have been made to extend the resistance of plants to stress associated with temperature and other causes as well as lengthening the shelf life of flowers, leaves and other portions from plants.
  • U.S. Patent No. 2,805,137 discloses a process for conditioning cut flowers by applying an effective amount of a composition comprising a phenol, a compound selected from the group consisting of carbonyl-containing compounds and compounds capable of being catabolized by plant enzymes to carbonyl- containing compounds and a compound selected from the group consisting of hydrazines, amines and quaternary ammonium compounds.
  • hydrazines and amines which are alleged to have antiseptic properties and the ability to lower the surface tension of water and therefore suited for use are mono and diamines such as methyl-amine, ethylamine, diamines such as ethylene diamine, trimethylenediamine, and polyamines such as triamino methane, tetramethylene-tetramine and hexamethylene-tetramine.
  • the phenol is present in a proportion by weight of 5-1200 parts, the carbonyl-containing compound from 5,000 to 50,000 parts and the hydrazine or amine at a level from 10-900 parts.
  • U.S. Patent No. 4,231 ,789 discloses the application of long chain polyamine compounds of the general formula H 2 N - R ⁇ -NH 2 wherein Ri represents a - (CH 2 ) n - where n represents an integer from 4-18 and various polyethylene polyamine amino derivatives thereof as a method for protecting crops from suffering various damages due to temperature, etc.
  • suitable amines within the formula include tetramethylenediamine, pentamethylenediamine, hexadecamethylene-diamine, spermidine and other polyamines.
  • the polyamine is diluted to a concentration generally in the range of 10 "4 to 10 "2 moles per liter and applied as an aqueous formulation.
  • the compounds presently available suffer from a number of drawbacks.
  • the triazole compounds paclabutrazol, uniconzole, triadimephon
  • the compounds have side effects. The most notable side effect being growth retardation (stunting) caused by the inhibition of gibberellin biosynthesis.
  • the present invention seeks to provide a method for inducing and or increasing tolerance to stress in plant material. At the very least the present invention seeks to provide an alternative to the methods and compounds that are presently available.
  • the present invention consists in a method for inducing stress tolerance in plant material, the method comprising the step of applying to plant material an effective stress-regulating amount of one or more compounds of the following formula (1) or functional derivative(s) thereof:
  • R-i , to R 5 are selected from the group consisting of hydrogen, loweralkyl, oxo, amino, carbonyl, halogen, thio, phosphate, sulfoxide, sulfone, deuterium, carboxyl, aldehyde, hydroxy, hydroxyloweralkyl, alkoxyloweralkyl, loweralkoxycarbonyl, loweracyloxyloweralkyi, actylloweralkyl, loweralkanoyl, loweralkylamino, diloweralkylamino, loweralkoxy, loweracyloxy, loweralkylthio, loweralkyl sulphonyl, loweralkyl sulphinyl, or cycloalkyl or cycloalkoxy having from 4 to 6 carbon atoms which is optionally substituted by loweralkyl, halogen, oxygen, hydroxy or loweralkoxy, such that the selection of R-i, to R 5 result in a compound capable of inducing stress
  • R 3 , and R 5 are both hydrogen while Ri, R 2 and R 4 are selected from the group consisting of hydrogen, loweralkyl, oxo, amino, carbonyl, halogen, thio, phosphate, sulfoxide, sulfone, deuterium, carboxyl, aldehyde, hydroxy, hydroxyloweralkyl, alkoxyloweralkyl, loweralkoxycarbonyl, loweracyloxyloweralkyi, actylloweralkyl, loweralkanoyl, loweralkylamino, diloweralkylamino, loweralkoxy, loweracyloxy, loweralkylthio, loweralkyl sulphonyl, loweralkyl sulphinyl, or cycloalkyl or cycloalkoxy having from 4 to 6 carbon atoms which is optionally substituted by loweralkyl, halogen, oxygen, hydroxy or loweralkoxy.
  • Ri is hydrogen, a hydroxy or an acetyloxy group
  • R 2 is hydrogen or a lower alkyl group
  • R 3 is hydrogen or a sulfoxide group.
  • the active compound is selected from the group consisting of Benzoic acid, 2-Hydroxy 5-sulfobenzoic acid (Sulfosalicylic acid), 2- Hydroxy Benzoic acid (Salicylic Acid), 2-Hydroxy 3-methylbenzoic acid (Methyl Salicylic acid) or 2-Acetyloxy Benzoic Acid (Acetyl Salicylic acid).
  • a functional derivative of an active compound is any derivative that is adapted to or capable of inducing stress tolerance.
  • functional derivatives include any compound that may be converted or degraded to benzoic acid or salicylic acid.
  • active compounds may also be employed as esters or salts thereof and for purposes of this invention the derivative salt form is equivalent to and incorporated into the terminology benzoic acid equivalents or salicylic acid equivalents.
  • benzoic acid equivalents or salicylic acid equivalents The conversion of naturally occurring compounds to salts for application to plants is known and that technology is applicable to the utilisation of the active compounds described here. Examples of such salts include potassium benzoate, sodium benzoate and the like.
  • Preparation of the above compounds may be achieved by any method known in the art. In this respect most of the above compounds are known in the art and may be prepared by well-practiced prior art methods.
  • Active compounds employed in the method of the present invention may be applied to various forms of plant material including, for example, whole plants such as seedlings and portions thereof such as cuttings, plant tissues or organs (in vitro and ex vitro) and cells, protoplasts, fruit, flowers, seeds and microspore cultures.
  • the method is applied to un-harvested whole plants.
  • the effective stress-regulating amount of active compound delivered to a plant material should be sufficient to exert or effect desired protection of the plant material to the stress that may be anticipated.
  • Such effective stress-regulating amounts will vary not only with the particular active compound selected for application, but also with the level of induced stress tolerance to be achieved, the species of plant being treated and its stage of development, and whether a permanent or transient regulating effect is sought.
  • an effective stress-regulating amount of active compound include, for example, the plant growth medium, the manner in which the treatment is to be applied, weather conditions such as temperature or rainfall, the amount and quantity of water absorbed by the plant material, the concentration of the compound in solution, the surface area of the plant material exposed and the ease of transfer of the compound to the interior of the plant cells.
  • the active compound it should be understood that some compounds may be far more active than other compounds.
  • benzoic acid has been found to be particularly active at much lower concentrations than salicylic acid.
  • Field tests have also demonstrated that the effects of the active compounds may also vary from one plant species to another depending on the nature and the concentration of the compound used. Hence, some of the active compounds may be highly specific to certain plant species while others may not.
  • an effective stress-regulating amount of the active compounds should serve to induce stress tolerance in the plant material.
  • an effective stress- regulating amount of active compounds is a concentration of between approximately 0.001 mM and 1.0 mM. More preferably, an effective stress- regulating amount of active compounds is a concentration of between approximately 0.05mM and 0.75 mM. Desirably, the active compound concentration is between approximately 0.01 mM and 0.5mM. More specifically the active compound concentration is between approximately 0.1 mM and 0.5mM.
  • the stresses to which the present invention may induce tolerance may be varied.
  • the stress tolerance is one or more of the stress tolerances in the group comprising: desiccation tolerance, drought tolerance, temperature tolerance such as freezing tolerance and heat tolerance, salinity tolerance, post transplant stress tolerance, post harvest weight loss, post harvest multiple stress tolerance and herbicide tolerance.
  • the method of the present invention may be used to reduce and preferably prevent plant death (whole or part of) or growth inhibition of seed derived, somatic embryo derived or micropropagated (tissue/cell culture derived) plants or plants derived from cuttings, which are exposed to stresses after transplanting and prior to complete plant establishment, as well as after establishment.
  • induction of stress tolerance may be achieved by application of the active compounds to plants in various stages of development.
  • the active ingredient can be applied to the soil habitat of the plant or directly to the plant in the seedling stage, flowering stage or fruiting stage and the like or can be applied sequentially to plants at more than one stage of development.
  • Such application may be made directly to one or more of the plant's parts, such as stems, leaves, flowers, fruit, seeds or the like.
  • the application is made by spraying or drenching or imbibing seeds or by irrigation of the plants using conventional techniques.
  • the active compounds are applied throughout the life of a plant as a hardening method to prevent injury or death by exposure to stress at any time of the plant's life cycle.
  • the method of the present invention may enhance the post harvest shelf life of the plant material (stems, leaves, fruits etc).
  • the method of the present invention may also be used to enhance cryopreservation and cold storage ability of plant material such as plant tissues.
  • seeds may be imbibed in one or more of the active compounds sowed or dried prior to planting. Applicant believes that other hardening treatments such as heat shock or chilling treatment when used in conjunction with the active compounds enhance the stress tolerance induced.
  • a method for inducing stress tolerance in plant material comprising the steps of: (i) subjecting a plant to heat shock or chilling treatment; and (ii) applying to a plant material an effective stress-regulating amount of benzoic acid or a functional derivative thereof.
  • Active compounds may be applied as a single compound (diluted to appropriate levels with a suitable dilution agent) or as a plurality of active compounds. Where a plurality of active compounds are employed they may be applied individually or in combination.
  • salicylic acid and acetyl salicylic acid may be formulated to be released in combination or alternatively they may be formulated to be released independently of each other. If formulated for independent release either salicylic acid or acetyl salicylic acid may be prepared to be released immediately or shortly after application to plant material while the other chemical may be formulated in a slow release applicator to ensure continual release of the other active compound over a long period of time.
  • the rate of application will depend on a number of factors, such as the amount of stress that the plant is likely to be subjected to or is subjected to, environmental conditions, type of plant species and the like.
  • the timing of the application and rate of application appear to bear a relationship to one another and to the plant species to which the compounds are applied, such that the rate of application and the timing thereof bear a relationship to the result observed.
  • the compounds are applied in combination with one or more application vehicles.
  • the prepared composition must contain and be capable of releasing an effective stress tolerant amount of an active compound to exert or effect desired protection of the plant to the stress that may be anticipated.
  • the active compounds are applied to the plant material with at least one formulation auxiliary selected from the following groups: solid carriers; solvents or dispersing agents; surfactants (wetting agents and emulsifiers); dispersants (without surfactant action); and stabilisers.
  • the active compounds can be prepared into customary formulations, such as dusts, powders, granules, solutions, emulsions, suspensions, emulsifiable concentrates, pastes and the like.
  • the active compounds are water-insoluble they can be formulated following methods customary for water-insoluble compounds, using the known formulation auxiliaries.
  • the compositions can be prepared in a manner known per se, for example by mixing the particular active substance with solid carriers, by dissolving or suspending in suitable solvents or dispersing agents, if desired with the use of surfactants as wetting agents or emulsifiers and/or disperstants, or by diluting of already prepared emulsifiable concentrates with solvents or dispersing agents.
  • the active compounds of this invention will be applied in the form of a concentrate that can be readily extended with an inert carrier prior to application to the plants.
  • Concentrates in solid form are, for example, water soluble powders consisting of finely divided solids such as calcium silicate, surfactant and from about 1-95% or more by weight of the active ingredient which are diluted with water prior to applying to the plants.
  • the active compounds may be applied as an aqueous solution to the plant sur ace to permit absorption of the compounds into the plant.
  • the concentration of active compound in the formulation may vary widely, e.g. from 0.0001 to 99%.
  • the active compounds when applied in liquid form are mixed with a solvent, surfactant, emulsifier, defoamer and/or additive and about 0.0001 to 95% by weight of the formulation is active ingredient.
  • the concentration of active compound in the formulation will vary from about 0.0001 to 70%.
  • the concentration of active compound in the formulation will vary from about 0.0001 to 50% and more specifically between about 0.0001 and 25%. In a particular example the concentration will vary between 0.0001 and 1.0%.
  • the aqueous solution may also be prepared as a liquid concentrate that can be diluted with water to provide a composition suitable for application to plants.
  • Some of these active compounds are active at very low dosages and therefore their ability to inhibit stress should not be confused with the herbicidal properties that have been observed when some of the compounds are applied at higher concentrations.
  • the active compounds may be applied to the plant material impregnated on finely divided or granular inorganic or organic carriers such as attapulgite clay, sand vermiculite, corn cobs, activated carbon or other granular carriers known to the art.
  • the impregnated granules may then be spread on the soil.
  • the active compounds may be formulated, for example, as a wettable powder by impregnating an inactive powdered carrier to which a surface-active dispersing agent has been added.
  • the active compounds can be mixed with a solid carrier, for example by grinding them together.
  • the solid carrier can be impregnated with a solution or suspension of the active substance, and the solvent or dispersing agent is then removed by evaporation, heating or filtering off under reduced pressure.
  • Such compositions in the form of powders can be rendered readily wettable with water by adding surfactants or dispersants, so that they can be converted into aqueous suspensions which are suitable, for example, as compositions for spraying.
  • the wettable powder may then be dispersed in water and sprayed on plants, or the soil surface, or plants to be prepared for harvesting.
  • an emulsifiable concentrate may be prepared by dissolving the active agents in a suitable solvent to which a surface- active dispersing agent has been added.
  • the emulsifiable concentrate may then be dispersed in water and applied by spraying.
  • solid carriers natural minerals, such as chalk, dolomite, limstone, clays and silica and their salts, for example kieselguhr, kaolin, bentonite, talc, attapulgite or montmorillonite; synthetic minerals such as highly disperse silica, aluminia or silicates; organic substances such as cellulose, starch, urea or synthetic resins; and fertilisers such as phosphates or nitrates.
  • Such carriers can be, for example, in the form of powders or granules.
  • solvents or dispersing agents aromatic substances such as benzene, toluene, xylene and alkylnaphthalenes; chlorinated aromatic substances and chlorinated aliphatic hydrocarbons such as chlorobenzene, chloroethylenes or methylene chloride; aliphatic hydrocarbons such as cyclohexane or parafins, for example mineral oil fractions; alcohols such as butanol or glycol and their ethers and esters; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone; and strongly polar solvents or dispersing agents, such as dimethylformamide, N-methylpyrrolidone or dimethyl sulfoxide (solvents of these types preferably have flash points of at least 30°C and boiling points of at least 50°C), or water.
  • aromatic substances such as benzene, toluene, xylene and alkylnaphthalen
  • Suitable solvents or dispersing agents are also so-called liquefied gaseous extenders or carriers, which are products that are gaseous at room temperature and under atmospheric pressure.
  • liquefied gaseous extenders or carriers which are products that are gaseous at room temperature and under atmospheric pressure.
  • aerosol propellants such as halohydrocarbons, for example dichlorodifluoromethane.
  • the surfactants can be non-ionic compounds such as: condensation products of fatty acids, fatty alcohols or fat-substituted phenols with ethylene oxide; fatty acid esters and fatty acid ethers of sugars or polyhydric alcohols; the products which are obtained from sugars or polyhydric alcohols by condensation with ethylene oxide; block polymers of ethylene oxide and propylene oxide; or alkyldimethylamine oxides.
  • the surfactants can also be anionic compounds such as: soaps; fatty sulfate esters, for example sodium dodecyi sulfate, sodium octadecyl sulfate or sodium cetyl sulfate; alkylsulfonates, arylsulfonates or fatty aromatic sulfonates, such as alkylbenzenes sulfonates, for example calcium dodecylbenzenesulfonate or butylnaphthalenesulfonates; or more complex fatty sulfonates, for example the amide condensation products of oleic acid and N-methyltaurine, or the sodium sulfonate of dioctyl succinate.
  • the surfactants can be cationic compounds such as alkyldimethylbenzylammonium chlorides, dialkyldimethylammonium chlorides, alkylmethylammonium chlorides or ethoxylated ammonium chlor
  • Suitable dispersants are mainly the following: lignin, sodium slats and ammonium salts of ligninsulfonic acids, sodium salts and ammonium salts of sulfonated polycondensation products from naphthalene and formaldehyde, or suifite waste liquors.
  • Examples which can be employed as dispersants which are particularly suitable as thickeners or sedimentation inhibitors are methylcellulose, carboxymethylcellulose, hydroxyethylcellulose, polyvinyl alcohol, alginates, caseinates or blood albumin.
  • Suitable stabilisers are: acid-binding agents, for example epichiorohydrin, phenyl glycidyl ethers or soya epoxides; antioxidants, for example gallic esters or butylhydroxytoluene; UV absorbers, for example substituted be ⁇ zophenones, diphenylacrylonitrilic esters or cinnamic esters; or deactivators, for example salts of ethylenediaminotetraacetic acid, or polyglycols.
  • acid-binding agents for example epichiorohydrin, phenyl glycidyl ethers or soya epoxides
  • antioxidants for example gallic esters or butylhydroxytoluene
  • UV absorbers for example substituted be ⁇ zophenones, diphenylacrylonitrilic esters or cinnamic esters
  • deactivators for example salts of ethylenediaminotetraacetic acid, or polyglycols
  • compositions in addition to the fore mentioned active compounds may also be applied to the plant material in conjunction with the active compounds.
  • Such compounds may be mixed with or included in, for example, insecticides, acaricides, nematicides, molluscicides, bactericides, fungicides, herbicides, plant growth regulators, fertilisers and trace element sources.
  • Such combined compositions are suitable for broadening the spectrum of action.
  • Seeds were also imbibed in the above solutions for 24 h and planted as above and plants were exposed to stress 21 days after planting.
  • Plants were chilled at 1°C in a growth chamber for 2 days respectively to simulate chilling injury. All the benzoic acid treated plants at appropriate concentrations of BZA survived whereas all the control plants exhibited severe leaf and growing point injury (wilting, desiccation, chlorosis, necrosis in whole or part) often resulting in a failure of plants to maintain normal growth (See Tables 1 & 2).
  • Bean and tomato leaves were sprayed with 1mL of benzoic acid solution at varying solutions. The respective plants were then subjected to chilling, heat and drought in accordance with the above methods. All the benzoic acid treated plants at appropriate concentrations of BZA survived whereas all the control plants exhibited severe leaf and growing point injury (wilting, desiccation, chlorosis, necrosis in whole or part) often resulting in a failure of plants to maintain normal growth (See Tables 3 & 4).
  • Bean and tomato seedlings were treated with benzoic acid and the pots were saturated with 200 mM NaCl for beans and 800 mM for tomato. Treated plants survived and did not display any injury 3 days after the treatment. Control plants were wilted (See Table 5).
  • Table 1 Bean plants were grown from seeds imbibed (SI) in solutions for 24 hours or 17 day old plants were soil drenched (SD) with 20mL of solution. Plants were exposed to stress at specified days after benzoic acid treatment.
  • Table 2 Tomato plants were grown from seeds imbibed (SI) in solutions for 24 hours or 17 day old plants were soil drenched (SD) with 20mL of solutions. Plants were exposed to stress at specified days after benzoic acid treatment.
  • Table 3 Bean plants were sprayed with 1mL of benzoic acid solution at varying concentrations. The plants were then subjected to chilling, heat and drought in accordance with the above methods
  • Table 4 Tomato plants were sprayed with 1mL of benzoic acid solution at varying solutions. The plants were then subjected to chilling, heat and drought in accordance with the above methods
  • Table 6 Gramaxone treatment: 8 days after soil drenching with BZA, the plants were sprayed using a hand held sprayer, with gramaxone (500 ⁇ L/L). Each plant received 1mL of herbicide solution. Damaged leaf area was estimated as a percentage of total.
  • Bean plants were treated with benzoic acid at 0.1 mM concentration 10 days before harvesting and the weight loss was monitored. The treated pods lost 25% less weight over 6 days at room temperature.
  • Solute (electrolyte) leakage 10 leaf discs from bean and tomato plants were taken and incubated in 5ml of deionized water and the conductivity of the solution was measured using a conductivity meter. The tubes containing leaf discs were heated in a water bath at 95°C for 5 min to kill all cells. The conductivity of the solution was recorded as a total and is illustrated in table 7.
  • Seeds were also imbibed in the above solutions for 24 h and planted as above and plants were exposed to stress 21 days after planting.
  • Plants were chilled at 1°C in a growth chamber for 2 days respectively to simulate chilling injury. All the 2-hydroxy 5-sulfobenzoic acid treated plants at appropriate concentrations of SSA survived whereas all the control plants exhibited severe leaf and growing point injury (wilting,- desiccation, chlorosis, necrosis in whole or part) often resulting in a failure of plants to maintain normal growth (See Tables 8 & 9).
  • Bean and tomato seedlings were treated with 2-hydroxy 5 sulfobenzoic acid and the pots were saturated with 200mM NaCl for beans and 800mM for tomato. Treated plants survived and did not display any injury 3 days after the treatment. Control plants were wilted (See Table 10). Bean seedlings were sprayed with 500 ul per litre Gramoxone 250TM, a commercial herbicide (active ingredient is paraquat dichloride). Control plants displayed necrotic lesions typical of paraquat injury within 24 h. Treated plants did not display any injury symptoms at this time (See Table 11 ).
  • Table 8 Bean plants were grown from seeds imbibed (SI) in solutions for 24 hours or 17 day old plants were soil drenched (SD) with 20mL of solutions. Plants were exposed to stress at specified days after Sulfosalicylic acid (SSA) treatment.
  • SI seeds imbibed
  • SD soil drenched
  • SSA Sulfosalicylic acid
  • Table 9 Tomato plants were grown from seeds imbibed (SI) in solutions for 24 hours or 17 day old plants were soil drenched (SD) with 20mL of solutions. Plants were exposed to stress at specified days after Sulfosalicylic acid (SSA) treatment. r
  • Table 11 Gramaxone treatment: 8 days after soil drenching with SSA, the plants were sprayed using a hand held sprayer, with gramaxone (500 ⁇ L/L). Each plant received 1 mL of herbicide solution. Damaged leaf area was estimated as a percentage of total.
  • Seeds were also imbibed in the above solutions for 24 h and planted as above and plants were exposed to stress 21 days after planting.
  • Bean seedlings were treated with salicylic acid and the pots were saturated with 200 mM NaCl. Treated plants survived and did not display any injury. Control plants displayed salt injury 24 h after the treatment and died 8 days after salt treatment.
  • Table 12 Bean plants were grown from seeds imbibed (SI) in solutions for 24 hours or 17 day old plants were soil drenched (SD) with 20mL of solutions. Plants were exposed to stress at specified days after salicylic acid treatment.
  • SI seeds imbibed
  • SD soil drenched
  • Table 13 Tomato plants were grown from seeds imbibed (SI) in solutions for 24 hours or 17 day old plants were soil drenched (SD) with 20mL of solutions. Plants were exposed to stress at specified days after salicylic acid treatment.
  • Table 14 Corn plants were grown from seeds imbibed (SI) in solutions for 24 hours or 17 day old plants were soil drenched (SD) with 20mL of solutions. Plants were exposed to stress at specified days after salicylic acid treatment.
  • SI seeds imbibed
  • SD soil drenched
  • Table 15 Bean plants were sprayed with 1mL of salicylic acid solution at varying solutions. The plants were then subjected to chilling, heat and drought in accordance with the above methods
  • ASA acetyl salicylic acid
  • Seeds were also imbibed in the above solutions for 24 h ⁇ and planted as above and plants were exposed to stress 21 days after planting.
  • Table 16 _Bean plants were grown from seeds imbibed (SI) in solutions for 24 hours or 17 day old plants were soil drenched (SD) with 20mL of solutions. Plants were exposed to stress at specified days after acetyl salicylic acid treatment.
  • Table 17 _Tomato plants were grown from seeds imbibed (SI) in solutions for 24 hours or 17 day old plants were soil drenched (SD) with 20mL of solutions. Plants were exposed to stress at specified days after acetyl salicylic acid treatment.
  • Table 18 _Com plants were grown from seeds imbibed (SI) in solutions for 24 hours or 17 day old plants were soil drenched (SD) with 20mL of solutions. Plants were exposed to stress at specified days after ASA treatment.
  • Table 19 Bean leaves were sprayed with 1mL of acetyl salicylic acid solution at varying solutions. The plants were then subjecte to chilling, heat and drought in accordance with the above methods
  • Bean seedlings were treated with acetyl salicylic acid and the pots were saturated with 200 mM NaCl. Treated plants survived and did not display any injury. Control plants displayed salt injury 24 h after the treatment and died 8 days after salt treatment.
  • Solute (electrolyte) leakage 10 leaf discs from bean and tomato plants were taken and incubated in 5mL of deionized water and the conductivity of the solution was measured using a conductivity meter. The tubes containing leaf discs were heated in a water bath at 95C for 5 min to kill all cells. The conductivity of the solution was recorded as a total and is illustrated in Table 22. Treated leave discs exhibited lower solute leakage than untreated plants indicating that the cellular integrity of the ASA treated leaf discs was greater than untreated leaf discs.
  • Table 20 Height of 14 day old bean plants, grown from seeds imbibed in acetyl salicylic acid solution.
  • Table 21 Height of 21 day old bean plants soil drenched with acetyl salicylic acid at 14 days of age.
  • Microsomal membranes were isolated from bean leaves, 7 days after acetyl salicylic acid treatment (soil drench), and the lipid transition temperature of the membrane was measured using differential scanning calorimetry (see Table 23).
  • Table 23 Differential Scanning Calorimetry: microsomal membranes were isolated from bean leaves, 7 days after ASA treatment (soil drench), and the lipid transition temperature of the membrane was measured using differential scanning calorimetry.
  • Table 24 Eucalyptus marginata seeds were sterilized and germinated in vitro in the dark for 2 weeks and seedlings were incubate in 0.5 mM solution of ASA for 3 days. The leaf petioles were excised and 1cm sections were cultivated on media containing 1/2 MS nutrients (Murashige, T. and Skoog, F., (1962) Physiologia Plantarum, 15:473-499), vitamins and 10 ⁇ M Thidiazuron. Tissue browning was monitored.
  • Geranium cv Elite Red was sprayed with 0.5 mM ASA. One week later leaf petioles were harvested, sterilized and cultured on media containing 1/2 MS nutrients (Murashige, T. and Skoog F., (1962) Physiologia Plantarum, 15:473-499), vitamins and 10 ⁇ M Thidiazuron.
  • the tissue browning was visually estimated using these classifications.
  • Seeds were also imbibed in the above solutions for 24 h and planted as above and plants were exposed to stress 21 days after planting.
  • Beans plants were sprayed with 1mL of methyl salicylic acid solution at varying concentrations. The respective plants were then subjected to chilling, heat and drought in accordance with the above methods. All the methyl salicylic acid treated plants at appropriate concentrations of MSA survived whereas all the control plants exhibited severe leaf and growing point injury (wilting, desiccation, chlorosis, necrosis in whole or part) often resulting in a failure of plants to maintain normal growth (see Table 29).
  • Table 26 Bean plants were grown from seeds imbibed (SI) in solutions for 24 hours or 17 day old plants were soil drenched (SD) with 20mL of solutions. Plants were exposed to stress at specified days after methyl salicylic acid treatment.
  • SI seeds imbibed
  • SD soil drenched
  • Table 27 Tomato plants were grown from seeds imbibed (SI) in solutions for 24 hours or 17 day old plants were soil drenched (SD) with 20mL of solutions. Plants were exposed to stress at specified days after methyl salicylic acid treatment.
  • Table 28 Corn plants (cv. Honeysweet) were grown from seeds imbibed (SI) in solutions for 24 hours or 17 day old plants were so drenched (SD) with 20mL of solutions. Plants were exposed to stress at specified days after methyl salicylic acid treatment.
  • Table 29 Bean plants (cv garden bounty)were sprayed with 1mL of methyl salicylic acid solution at varying solutions. The plants were then subjected to chilling, heat and drought in accordance with the described methods.
  • Tuart Eucalyptus gomphocephala leaves were sprayed with varying concentrations of methyl salicylic acid and then subjected to heating at 58C for 2.5 hours.
  • Application of MSA and ASA at 0.5mM substantially halted injury to heat treated leaves (see Table 30)
  • a branch containing leaves of the tree Corymbia ficifolia (Eucalyptus ficifolia) of Eucalyptus and geranium (cv Elite Red) were treated with methyl salicylic acid and petiole sections were harvested and cultured on sterile nutrition media containing growth regulators auxins and cytokinins and thidiazuron and monitored the tissue browning. Substantial reduction in tissue browning and death during excision and in culture was observed in acetyl salicylic acid treated plants (see Tables 31 & 32).
  • agricultural and horticultural compositions comprising as an active ingredient an effective stress-regulating amount of at least one of the above mentioned compounds may be very useful for treating agricultural, forestry and horticultural plants which may be exposed to state of stresses, for example, in salty regions such as on reclaimed land, coast land or a region closed by a desert susceptible to be damaged by a drought, or in regions where sudden chills or excessive heat are prevalent or where transplant trauma may be significant in reducing plant vigour or survival.
  • Table 30 Tuart (Eucalyptus gomphocephala) leaves were sprayed with varying concentrations of methyl salicylic acid and then subjected to heating at 58°C for 2.5 hours
  • Table 31 Branch of leaves of Corymbia ficifolia (Eucalyptus ficifolia) tree was sprayed with 0.5 mM MSA. One week after spraying the leaf petioles were sterilized and 1 cm sections were cultured on agar medium containing 1/2 MS nutrients (Murashige, T. and Skoog, F., (1962) Physiologia Plantarum, 15:473-499), vitamins and growth regulators, 0.5 ⁇ M Benzylaminopurine. Tissue browning and survival was monitored.
  • Geranium cv Elite Red was sprayed with 0.5 mM MSA. One week later leaf petioles were harvested, sterilized and cultured on media containing 1/2 MS (Murashige, T. and Skoog, F., (1962) Physiologia Plantarum, 15:473-499), vitamins and 10 ⁇
  • the tissue browning was visually estimated using these classifications.

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  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
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  • Wood Science & Technology (AREA)
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Abstract

L'invention concerne un procédé permettant d'induire une tolérance à la tension dans des matières végétales. Le procédé consiste à appliquer au matières végétales une quantité régulatrice de tension efficace d'un ou plusieurs composés actifs de formule (1) ou d'un dérivé fonctionnel, dans laquelle R1, R2, R3, R4 et R5 sont sélectionnés dans le groupe constitué d'hydrogène, alkyle inférieur, oxo, amino, carbonyle, halogène, thio, phosphate, sulfoxyde, sulfone, deutérium, carboxyle, aldéhyde, hydroxy, hydroxylalkyle inférieur, alcoxy alkyle inférieur, alcoxy carbonyle inférieur, acyloxy inférieur alkyle inférieur, actylalkyle inférieur, alcanoyle inférieur, alkylamino inférieur, dialkylamino inférieur, alcoxy inférieur, acyloxy inférieur, alkythio inférieur, sulphonyle inférieur, sulphinyle alkyle inférieur ou cycloalkyle ou cycloalcoxy présentant entre 4 et 6 atomes de carbone qui est éventuellement substitué par un alkyle inférieur, halogène, oxygène, hydroxy ou alcoxy inférieur de manière que la sélection de R1 à R5 se traduit par un composé capable d'induire une tolérance à la tension dans les matières végétales.
PCT/AU1998/000949 1997-11-14 1998-11-13 Procede permettant d'induire une tolerance a la tension dans des matieres vegetales Ceased WO1999025191A1 (fr)

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Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001022822A1 (fr) * 1999-09-24 2001-04-05 Steve Wood Methode permettant de renforcer l'immunite de vegetaux et d'animaux
US6241795B1 (en) 1999-04-16 2001-06-05 Miller Chemical And Fertilizer Corporation Soluble fertilizer formulation
GB2357971A (en) * 1999-12-23 2001-07-11 Novartis Ag Protection of plants against microorganism attack
WO2001072130A3 (fr) * 2000-03-29 2002-03-28 Wisconsin Alumni Res Found Procedes destine a ameliorer l'etat phytosanitaire des plants, a les proteger des alterations associees au stress biotique et abiotique et a ameliorer la reparation des plants alteres par un tel stress
FR2826547A1 (fr) * 2001-06-29 2003-01-03 Agronomique Inst Nat Rech Utilisation en phytoprotection d'esters d'acide salicylique et de leurs associations avec des elicitines
WO2004084631A1 (fr) * 2003-03-26 2004-10-07 Bayer Cropscience Gmbh Utilisation de composés aromatiques hydroxy comme phytoprotecteurs
WO2007042795A1 (fr) * 2005-10-12 2007-04-19 Plant Impact Plc Composition agricole
US8138118B2 (en) * 2003-08-05 2012-03-20 Bayer Cropscience Ag Use of hydroxyaromatics as safeners
US8545816B2 (en) * 2005-03-21 2013-10-01 Ferrer Internacional, S.A. Benzoic acid ester compounds, compositions, uses and methods related thereto
EP2796042A1 (fr) * 2013-04-23 2014-10-29 Albert-Ludwigs-Universität Freiburg Composés favorisant la croissance des plantes
US9840480B2 (en) 2013-05-28 2017-12-12 Empire Technology Development Llc Humic acid derivatives and methods of preparation and use
US9932319B2 (en) 2013-05-28 2018-04-03 Empire Technology Development Llc Antioxidant humic acid derivatives and methods of preparation and use
US10106570B2 (en) 2013-06-28 2018-10-23 Empire Technology Development Llc Edible plasticizers for food and food packaging films
US11304388B2 (en) * 2016-04-28 2022-04-19 Seoul Viosys Co., Ltd. Method for promoting growth and bioactive substances of Crepidiastrum denticulatum

Citations (1)

* Cited by examiner, † Cited by third party
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AU5237096A (en) * 1995-05-23 1996-12-05 Sst Australia Pty Ltd Plant growth regulating method and composition

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AU5237096A (en) * 1995-05-23 1996-12-05 Sst Australia Pty Ltd Plant growth regulating method and composition

Non-Patent Citations (1)

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Title
DERWENT ABSTRACT, Accession No. 93-150079/18, Class C01; & SU 1732901 A (A MED PLANTS PHYSIOLOGY BIOCHEM INST) 15 May 1992. *

Cited By (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6241795B1 (en) 1999-04-16 2001-06-05 Miller Chemical And Fertilizer Corporation Soluble fertilizer formulation
WO2001022822A1 (fr) * 1999-09-24 2001-04-05 Steve Wood Methode permettant de renforcer l'immunite de vegetaux et d'animaux
GB2357971A (en) * 1999-12-23 2001-07-11 Novartis Ag Protection of plants against microorganism attack
US6559099B1 (en) 2000-03-29 2003-05-06 Wisconsin Alumni Research Foundation Methods for enhancing plant health, protecting plants from biotic and abiotic stress related injuries and enhancing the recovery of plants injured as a result of such stresses
US7101828B2 (en) 2000-03-29 2006-09-05 Wisconsin Alumni Research Foundation Methods for enhancing plant health, protecting plants from biotic and abiotic stress related injuries and enhancing the recovery of plants injured as a result of such stresses
WO2001072130A3 (fr) * 2000-03-29 2002-03-28 Wisconsin Alumni Res Found Procedes destine a ameliorer l'etat phytosanitaire des plants, a les proteger des alterations associees au stress biotique et abiotique et a ameliorer la reparation des plants alteres par un tel stress
FR2826547A1 (fr) * 2001-06-29 2003-01-03 Agronomique Inst Nat Rech Utilisation en phytoprotection d'esters d'acide salicylique et de leurs associations avec des elicitines
WO2003001912A1 (fr) * 2001-06-29 2003-01-09 Institut National De La Recherche Agronomique (Inra) Utilisation en phytoprotection d'esters d'acide salicylique et de leurs associations avec des elicitines.
WO2004084631A1 (fr) * 2003-03-26 2004-10-07 Bayer Cropscience Gmbh Utilisation de composés aromatiques hydroxy comme phytoprotecteurs
JP2006521311A (ja) * 2003-03-26 2006-09-21 バイエル クロップサイエンス ゲーエムベーハー 芳香族ヒドロキシ化合物の薬害軽減剤としての使用
EA014910B1 (ru) * 2003-03-26 2011-02-28 Байер Кропсайенс Аг Применение гидроксиароматических соединений в качестве защитных веществ для культурных и полезных растений, способ защиты полезных и культурных растений от фитотоксических побочных воздействий агрохимикатов и средство защиты растений на их основе
US8138118B2 (en) * 2003-08-05 2012-03-20 Bayer Cropscience Ag Use of hydroxyaromatics as safeners
US8545816B2 (en) * 2005-03-21 2013-10-01 Ferrer Internacional, S.A. Benzoic acid ester compounds, compositions, uses and methods related thereto
WO2007042795A1 (fr) * 2005-10-12 2007-04-19 Plant Impact Plc Composition agricole
US8137429B2 (en) 2005-10-12 2012-03-20 Plant Impact Plc Agricultural composition
EP2796042A1 (fr) * 2013-04-23 2014-10-29 Albert-Ludwigs-Universität Freiburg Composés favorisant la croissance des plantes
WO2014173936A3 (fr) * 2013-04-23 2015-02-19 Albert-Ludwigs-Universität Freiburg Composés favorisant la croissance de plante
US9840480B2 (en) 2013-05-28 2017-12-12 Empire Technology Development Llc Humic acid derivatives and methods of preparation and use
US9932319B2 (en) 2013-05-28 2018-04-03 Empire Technology Development Llc Antioxidant humic acid derivatives and methods of preparation and use
US10106570B2 (en) 2013-06-28 2018-10-23 Empire Technology Development Llc Edible plasticizers for food and food packaging films
US11304388B2 (en) * 2016-04-28 2022-04-19 Seoul Viosys Co., Ltd. Method for promoting growth and bioactive substances of Crepidiastrum denticulatum

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